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The hubs are apparently unable to terminate a 'live' connection. They do seem to be able to stop a new connection after the cut-off time though. The solution would be to invest in a proper router.
I use a third party router and it will terminate a running connection, wired and wireless, as well as prevent a new one once the cut-off time is reached.
Yes. If the device is connected to as you say youtube or anywhere else the when the time comes nothing will happen. But if for example you set the cut-off for 9PM and he tries to connect after that time then the hub should prevent the device connecting.
Theoretically it should make no difference what the device is, it should be prevented from making a new connection.
How well the hubs actually do this, not allowing a new connection, I personally can't say as I never use them.
If your time settings are correct for all devices you want to restrict you should not have to re-enter them. Just remember to Save any changes before leaving the page on the hub.
Other things you can do are disable ipv6 on his phone and manually assign the same ip address on his phone as the router. In addition to this enter the phone's MAC address into the restricted settings too. In my opinion it shouldn't matter if he is connected or not. When the restriction kicks in it should kick him off. That is after all the whole point of it....
Have you tried what I suggested? In my opinion it could well be a ipv6 issue. Therefore simply disabling ipv6 on his phone could make all the difference. You mentioned assigning a single ipv4 address via the router, but to make doubly sure assign the same ip address actually on his phone, and like I said tieing it to his phone's MAC address should be the cherry on the top so to speak, making doubly certain. Let us know how you get on 🙂
IPv6 should make no difference if your router works properly. It should use the device ID to differentiate between devices connected to it. As shown below it should have all the details necessary IE: Name, IPv4 and IPv6 address(s) assigned as well as the MAC address. So IPv6 or IPv4 will make no difference. To a proper router